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The second and third look very well executed but I'm unsure of the mountain range of the second and the strange square divides in the third. These elements maybe technically correct for the style of the map (and I wouldn't know either) but I'm not a fan.

I really love the story this tells Tear. I think you did a good job capturing the flavor of old-to-modern and then post apocalyptic mapping styles. The only think that I see right off that is probably unrealistic is that the rivers are dead-on accurate from the first to the last. Accuracy tends to be a function of tech, and before the science was developed (or after it was forgotten), the ability to accurately establish the location of anything was lacking.

Accuracy tends to be a function of tech, and before the science was developed (or after it was forgotten), the ability to accurately establish the location of anything was lacking.

You are right, of course.
To be honest, I just did this for for the fun of it and didn't think up a whole lot of detail for the world's background.
On the other hand, since this is a completely fictional world, why not add some low-level magic into the equation?
I know, the old "a wizard did it" thing is kind of a lame excuse, but maybe some location-divination-thingy could have helped?
Just adding some food for thought here.